Scandium(III) Triflate-Catalyzed Reaction of Aroyl-Substituted Donor–Acceptor Cyclopropanes with 1-Naphthylamines: Access to Dibenzo[<i>c</i>,<i>h</i>]acridines

Abstract

The reaction of aroyl-substituted donor–acceptor (D–A) cyclopropanes with two equivalents of 1-naphthylamines in the presence of a catalytic amount of scandium(III) triflate provides access to dibenzo[c,h]acridines. The key steps of the transformation are the formation of nucleophilic ring-opening products from the D–A cyclopropanes and 1-naphthylamines and their subsequent fragmentation and cyclization. The method has a reasonable substrate scope, and the products are formed in 50–70% yields.

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